Versatile synthesis of tunable N,S-bridged-[1.1.1.1]-cyclophanes promoted by ester functions

We report herein a powerful and highly adaptable metal-free organic synthetic route to functionalized N,S-bridged-[1.1.1.1]-cyclophanes using an ester-promoted macrocyclisation step. The newly synthesized cyclophanes are obtained in good yields exhibiting (i) high solubility, allowing the possibility to enlarge the scope and chemistry for such macrocycles, (ii) a tunable cavity and (iii) orthogonal functional groups. (C) 2016 Elsevier Ltd. All rights reserved.

Keywords

Organic synthesis Macrocycles SNAr [1.1.1.1]-Cyclophanes

Domains

Chemical Sciences Organic chemistry

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Submitted on : Tuesday, February 7, 2017-10:55:32 AM

Last modification on : Friday, August 4, 2023-3:04:12 PM

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hal-01459073 , version 1 (07-02-2017)

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HAL Id : hal-01459073 , version 1
DOI : 10.1016/j.tet.2016.08.034

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Volodymyr Malytskyi, Vinicius Demetrio Da Silva, Olivier Siri, Michel Giorgi, Jean-Manuel Raimundo. Versatile synthesis of tunable N,S-bridged-[1.1.1.1]-cyclophanes promoted by ester functions. Tetrahedron, 2016, 72 (41), pp.6363-6367. ⟨10.1016/j.tet.2016.08.034⟩. ⟨hal-01459073⟩

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